


Cheek to Cheek

by caffeinechesters



Category: Supernatural
Genre: Body Horror, Dean in Hell, M/M, Torture
Language: English
Status: Completed
Published: 2013-12-04
Updated: 2013-12-04
Packaged: 2018-01-03 10:35:12
Rating: Mature
Warnings: Rape/Non-Con
Chapters: 1
Words: 1,298
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1069453
Author URL: https://archiveofourown.org/users/caffeinechesters/pseuds/caffeinechesters
Summary: <blockquote class="userstuff">
              <p>Alastair had to get the righteous man to pick up a blade in Hell, even if he had to get creative.</p>
            </blockquote>





	Cheek to Cheek

**Author's Note:**

> So this started out as a challenge to myself to try to write something dark and kind of smut-ish. Unbeta'd, so any grammar or spelling mistakes are my own, but if you find any please tell me.

Alastair felt redeemed when he saw Dean Winchester on his rack. John had been a miserable failure, a constant reminder how he lost his perfect score on breaking souls. But now, Dean was there (Daddy’s good little soldier) and he was not going to hold back. He had to break him. He had to make the righteous man pick up a blade before those damn angels got involved. Grinning to himself, he picked up a rusty Parisienne scoop placing it against his right eye.

“Hello Dean,” he purred, “We are going to have so much fun together.”

He flicked his wrist, removing the eye with just a little bit of the nerve still attached, and Alastair thought this might be what heaven feels like when he heard Dean’s scream. He knelt in front of Dean looking into his eyes, well eye and bloody socket, and told him, “If you want this to stop Dean-o, all you have to do is pick a blade and carve into other souls. So what do you say?” Dean spat in his face and glared as best as he could. This was going to be so satisfying when Dean’s soul breaks Alastair thought.

The next couple of years, Alastair dabbled in the various forms of physical torture. He had to admit the boy was stubborn just like his daddy, but even his daddy had problems when he took the form of Mary. He felt like wearing John to begin with, because hell, he spent a century with the guy; Alastair figured he knew every little sweet spot and cog that made John tick. When Dean-o drew in a breath and held it, he thought today was going to be the day.

“Hey Dean,” Alastair spoke, careful of the accent, “ I thought I told you look after Sammy. This is not looking after him being in hell is it?”

Dean gave a pained look, so Alastair goaded him more, “I also recall telling you that if you couldn’t save Sam, you’d have to kill him. Who is going to that now? If only you knew what your brother was doing topside.”

“You know the spiel Dean-o. You get off of the rack if you put souls on. Is today the day,” Alastair asked.

Dean gave him that aggravating shit eating grin before laughing at him. That day didn’t end well for Dean after all, but Alastair found a new appreciation of fileting his skin off and making a bouquet of roses from them. Alastair also found out that he loved growing roses out of Dean’s heart and Venus fly traps from his stomach, of which, he found it particularly amusing to feed the fly traps slivers of Dean’s sweetmeats and digits. They seemed to find Dean particularly tasty, too, and looked perkier and happier when his screams came out hoarse and jagged after screaming so long. Yes, he had found his perfect boy that he entertain himself for all of eternity, but he had to break him. It was such a shame, but it had to be done.

He spent the next decade or two trying various people in Dean’s life: Mary (it just pissed off more and made him uncooperative), John (good, but not the best), Cassie (he just looked resigned and wistful), and Sam. Little Sammy was the best weapon Alastair had. He had heard the rumors that the Winchester brothers held more than a brotherly affection for each other and he used that to advantage. Some days he was so close, he could feel the yes on the tip of Dean-o’s tongue, but instead would bite down on it and shake his head no.

Today though, he had a different idea since the normal physical and psychological torture wasn’t working after 30 years he would do something radical different from the normal hell torture. He slid into Sam’s skin and plastered on one darling Sammy’s best grins while walking up to Dean.

“Hey Dean,” he said, running a hand down his arm, “I thought we would try something different today.” Dean looked petrified with his eyes wide and bright. Alastair pressed his lips onto Dean’s, trying hard not to ravish him. Dean opened up quite easily after a few insistent kisses, pliant and soft, which is right where Alastair wants him to be. He works Dean up to incoherent babble, sucking, caressing, down his body, mouthing around the juts of Dean’s hipbones and inner thighs.

“Sam,” Dean rasped, “Please, Sam.” 

Yes, Alastair was getting close, just a bit further. He nosed along Dean’s erection, placing a few kisses along the way. 

“What do you want Dean,” Alastair grinned, “Tell me what you want and I’ll give you anything, but for today only.”

“I want you to fuck me, Sammy,” Dean panted out.

Alastair, being the ever professional, tried to contain his excitement. His favorite pet was soon going to be eternally his. 

“Okay, Dean. I can do that,” he responded, wrapping his lips around Dean’s dick.

Alastair worked methodically, sucking Dean off while fingering him open. And since Hell is pretty much, well, Hell he had to improvise with the lube, instead coating his fingers with sticky, partially congealed blood (Dean didn’t seem to mind). He continued to suck, and occasionally tongue Dean’s slit, until Dean was open and about to come. Alastair stopped, pulling off with a pop, and stood behind him nuzzling Dean’s neck while lubing up.

“Are you ready Dean,” Alastair whispered into Dean’s ear, “because I think you are.”

Dean whimpered out a breathy yes and he slid inside slow, finding ecstasy in the way Dean leaned back trying to speed him up. Alastair chuckled, thinking that he found heaven in hell, while he bottomed out. He set a slow, torturous pace actively avoiding hitting Dean’s prostrate because he wanted this to last (Alastair will admit this was mainly for him), but that quest of avoiding it was in vain after a few moments. Alastair thought Dean’s screams, all of them, were beautiful, but he wanted to compose a fucking aria of Dean’s moans and passion-drenched screams. However, like all good things, they must end. He felt Dean about ready to orgasm; he grabbed the base of Dean’s dick and stilled.

“Dean-o, you can come off the rack if you pick up a blade and torture souls. I am however going to sweeten the deal for today and today only,” Alastair murmured, “Become my apprentice and we can do this for all of eternity. He felt Dean shutter, his throat working, and when he finally spoke it was like crescendo; he had finally said yes. To reward Dean, he picked up the pace of his thrusts and matched his hand jacking off Dean to that rhythm. Yes, Alastair had found heaven in hell.

The next decade went far too quickly in Alastair’s eyes. Dean got more depraved with every new soul he torn into, the kid was a fucking natural at this. He taught Dean everything he knew, enjoying the slow fade of green eyes to inky black. He enjoyed that Dean finally got the finer things in Hell, like the joy of feeling someone break or the cultivating a garden in the expanse of the soul, but the best was that Dean would take Alastair anyway he pleased. His bed may be mostly blood, sweat, and semen at this point, but damn did it feel wonderful.

The angels are coming is all Alastair heard a moment before they arrived. He laughed at the head angel, Castiel, remarking, “You are about ten years too late, fellows. Dean is mine and belongs in hell.” 

Angels, though, what a bag a dicks. They took Dean topside despite his boy’s protests. They’ll meet again, though. He is sure of it.


End file.
